Lenny Bruce Pretended to Be Gay to Get Out of the Military
Corporal Maxwell Klinger is a character that you might recognize if you've ever watched the television series M*A*S*H, which is set in a military hospital during the Korean War. Klinger frequently wore women's attire with the intention of getting dismissed from the service under Section 8. He was jokingly pretending to be mentally ill, which would be justification for a medical and honorable discharge, but no one accepted it, so he just carried out his tasks while dressed as a woman. Lenny Bruce, a real-life comedian, served as a significant influence on the character.
Bruce allegedly "acted as a transvestite" in order to receive an honorable release from the military, according to some accounts, although that doesn't seem to be totally accurate. The character from M*A*S*H appears to be supporting the cross-dressing scenario, which may be a sanitized version of what Bruce actually did. Bruce claimed in letters that he pretended to be gay rather than a cross-dresser.
He would have needed to be both unfit for duty and not in a shameful fashion in order to get an honorable discharge. He told his doctors that he felt queer impulses as a result. His writing suggests that he told them that he was having trouble controlling these thoughts and that he utterly despised them, but they had emerged out of the blue. He claimed that despite wanting to have sex, he only ever kissed other soldiers. He basically portrayed it as a problem that he was pleading for assistance to solve. They complied, believing that an honorable discharge would "heal" him.